Southern Highlands Ski Vacations

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Flight and Ski hotel deals in Southern Highlands

Price found within the past 48 hours. Click for updated prices.
Quest Bella Vista

Quest Bella Vista

Bella Vista
CA $2,628
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Sydney (SYD)
9/10 Wonderful! (701 reviews)
Convenient location. Close to woolworths. Secure parking.

Reviewed on Aug 16, 2026

YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

Sydney Central Business District
CA $2,792
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Sydney (SYD)
8.2/10 Very good! (2,874 reviews)
Rydges Sydney Central

Rydges Sydney Central

Surry Hills
CA $2,689
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Sydney (SYD)
8.8/10 Excellent! (1,000 reviews)
Nice hotel, close to shopping and very well maintained. Comfortable room, nice bathroom. Only negative (small) was bed. Super soft so we sank into it. Otherwise comfortable stay

Reviewed on Aug 16, 2026

The Old Clare by Ode Hotels

The Old Clare by Ode Hotels

Chippendale
CA $2,860
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Sydney (SYD)
9.2/10 Wonderful! (584 reviews)
The Langham, Sydney

The Langham, Sydney

Millers Point
CA $3,067
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Sydney (SYD)
9.6/10 Exceptional! (999 reviews)
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5* Ski holidays in Southern Highlands

Price found within the past 48 hours. Click for updated prices.
Amora Hotel Jamison Sydney

Amora Hotel Jamison Sydney

Sydney Central Business District
CA $2,879
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Sydney (SYD)
9/10 Wonderful! (1,514 reviews)
Love this property

Reviewed on Aug 16, 2026

The Langham, Sydney

The Langham, Sydney

Millers Point
CA $3,067
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Sydney (SYD)
9.6/10 Exceptional! (999 reviews)
QT Bondi

QT Bondi

Bondi Beach
CA $3,269
per person
Oct 2 - Oct 5
just found
Roundtrip flight included
Toronto (YTO) to Sydney (SYD)
9.2/10 Wonderful! (767 reviews)
Great location. Staff were very kind and helpful. Nice room, comfy bed, great shower pressure. Loved having a washer/dryer and stove for cooking. Only thing missing was a pot.

Reviewed on Aug 5, 2026

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3 Night Ski holidays in Southern Highlands

Price found within the past 48 hours. Click for updated prices.
YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

Sydney Central Business District
CA $2,373
per person
Oct 26 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Sydney (SYD)
8.2/10 Very good! (2,874 reviews)
Rydges Sydney Central

Rydges Sydney Central

Surry Hills
CA $2,406
per person
Oct 26 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Sydney (SYD)
8.8/10 Excellent! (1,000 reviews)
Nice hotel, close to shopping and very well maintained. Comfortable room, nice bathroom. Only negative (small) was bed. Super soft so we sank into it. Otherwise comfortable stay

Reviewed on Aug 16, 2026

Ovolo Sydney Woolloomooloo, a Wyndham Hotel

Ovolo Sydney Woolloomooloo, a Wyndham Hotel

Woolloomooloo
CA $2,479
per person
Oct 26 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Sydney (SYD)
9.2/10 Wonderful! (1,001 reviews)
Great Room and Property Location!

Reviewed on Aug 16, 2026

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4 Night Ski holidays in Southern Highlands

Price found within the past 48 hours. Click for updated prices.
YEHS Hotel Sydney QVB

YEHS Hotel Sydney QVB

Sydney Central Business District
CA $2,470
per person
Oct 25 - Oct 27
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Sydney (SYD)
8.6/10 Excellent! (1,001 reviews)
Adina Apartment Hotel Bondi Beach Sydney

Adina Apartment Hotel Bondi Beach Sydney

Bondi Beach
CA $2,581
per person
Oct 25 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Sydney (SYD)
9.2/10 Wonderful! (1,178 reviews)
Both the girls at check in were first class and made my process so easy. A great place to stay in Bondi

Reviewed on Aug 10, 2026

Spicers Potts Point

Spicers Potts Point

Potts Point
CA $2,668
per person
Oct 25 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Sydney (SYD)
9.8/10 Exceptional! (155 reviews)
Class all the way and Phillip at reception was brilliant. The advice he gave regarding local restaurants was well received and accurate. The only disappointment was we had only one night there! We will be back!

Reviewed on Jun 8, 2026

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Plan the ultimate ski vacation in Southern Highlands

What are some benefits when booking ski vacations in Southern Highlands?

If you're interested in skiing, there's nothing quite like a ski vacation. These trips are designed to allow you to enjoy being on the slopes and relax in tranquil and convenient accommodations at the end of the day. Amenities on ski trips can be pretty upscale, so it's easy to relax in a hot tub or at a spa in between your skiing excursions. Plus, they can put you right next to the slopes. You'll even find a variety of different vacation types available whether you're looking for family friendly, cheap, or even last minute ski vacations.

How can I book the best ski vacation in Southern Highlands?

It is most important to implement the ski filter in your search when trying to find a ski vacation that will make you happy. Using the filter will automatically remove any entries that don't offer the skiing opportunities you want. After that, you'll need to think about what specifically you want from Southern Highlands, and think about the time of year that's best to visit.

How can I find cheap ski vacations?

Cheap ski vacations are readily available in Southern Highlands with some as cheap as CA $2,373. You can see the cheapest options by sorting your accommodation choices by price, which automatically puts the least-expensive results at the top of the list. You may also want to consider an accommodation with a kitchen, so you can cook instead of eating out.

Can I book ski packages?

Yes, ski packages are readily available throughout Southern Highlands. All you have to do is put in your travel dates and see what's available. When you book a ski package, you may be able to enjoy discounts with savings of up to 9 when you book your accommodation and your flight together.

What should I consider when booking family ski vacations?

The key to a successful family ski vacation is ensuring that your family is kept happy and entertained. Consider what your family members are interested in and the kind of vacation they want. If they have little skiing experience, for example, you may want to opt for an accommodation that offers ski lessons or a kid's club. Various slope difficulties may be essential in providing opportunities for everyone at Southern Highlands.

Can I book all-inclusive ski vacations in Southern Highlands?

Yes, all-inclusive ski trips are available and may be precisely what you're looking for. All you have to do is include the filter for all-inclusive stays, and your search results will only show the accommodations that provide this handy feature that allows you to plan your entire trip to Southern Highlands in advance.

What's the best time of year to plan a ski trip?

The apparent answer to when you should plan a ski trip is in winter, but other details are important too. If you book for Southern Highlands's high season around January and February, you'll likely find increased prices. It's generally best to opt for the early or late season in December and April, as prices tend not to be quite as high.

How can I find the best deals on ski packages in Southern Highlands?

When you're looking for cheap ski vacations, there are a few factors you can take advantage of to help get the best deals. Travelling during the off-season can be cheaper since there's more availability. However, the beginning and end of the season tend to be the most affordable for skiing.

Can I book a ski vacation that's fully refundable?

Being fully refundable is a feature you'll find on several accommodation packages in Southern Highlands. You can even search for it explicitly using a filter for full refundability.

Why should I book a ski vacation package with Expedia?

When you book with Expedia, you'll find everything you need for cheap ski vacations, luxury ski vacations and everything in between in one central location. You may even be able to enjoy discounts for booking your accommodation and your flight together with savings of up to 9. With Expedia Rewards, you can earn points towards your next booking.

Things to do

Highland Vines

Personalised wine tour experience in the beautiful NSW Southern Highlands

CA $241
per adult
Personalised wine tour experience in the beautiful NSW Southern Highlands
Sydney Wine Tasting & Southern Highlands with Pick up & drop off

Sydney Wine Tasting & Southern Highlands with Pick up & drop off

CA $445
per adult
Sydney Wine Tasting & Southern Highlands with Pick up & drop off
See all activities in Southern Highlands

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.